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Old Grafton Road Pleasant Prospect, Scarborough Tobago
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#3 of 14 B&Bs / Inns in Scarborough
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A beautiful clean guesthouse overlooking Grafton Beach in the lovely village of Pleasant Prospect. Four spacious double rooms with a shared bathroom, kitchen and living room. The large balcony offers a stunning view of the local area where guests can enjoy dinners together and relax in the hammocks with the ocean.
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Mads wrote a review Mar 2020
7 contributions
+1
Recently returned from another great stay at Two Seasons. My friends and I go Tobago annually, for carnival and always have a great stay at Two Seasons- the only place we will stay! The guest house is clean and has what you need for a relaxing, safe trip! The owner, Karin (Dales wife) is a lovely host and is always very helpful and friendly! Karin recommended a taxi driver-Chris Local 463 9018. UK no. ±1868 dialling access. Thanks to Karin we got introduced to Chris who is soooo reliable its unbelievable! We used his taxi a lot to get around and to the airport when we sadly had to go home!!! The guest house is a 10 minute walk to the beach My Irvine (pics inc). There is a shop and restaurants downstairs and also a bar across the road! Two seasons is a peaceful, clean place with comfortable rooms with all you need at the guest house. The balcony area is my favourite. Relax in a hammock and take in the views. We will be back! Thank you Karin!!
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Date of stay: February 2020
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This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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Lotte D wrote a review Jan 2018
Utrecht, The Netherlands3 contributions2 helpful votes
Dale's self-built wooden home is a place to enjoy life in general. Put up your hammock or put yourself in one of Dale's, cook some tea and take a slice of his crispy fresh homemade bread before you start your day in the sea surfing away or in the jungle scooping up some mangos. Had an awesome time, the best in Tobago, while I was at his home. Good chatting as well. A place to be yourself and make a few good friends. Only note; bring earplugs as the barmanager across the street likes to wallow at loud music sometimes;) Don't think twice about going here! Just enjoy it.
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Date of stay: January 2018
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Trip type: Travelled solo
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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Sally D wrote a review Apr 2017
London, United Kingdom3 contributions1 helpful vote
Dale is a brilliant host, very friendly and full of stories and knowledgeable about the island! I spent a several hours hanging out in a hammock on the beautiful deck chatting to him with a requisite rum in hand.. He makes awesome bread too..the place is simple, very clean with a cosy vibe and you will meet like minded well travelled people with a relaxed no fuss demeanour! Highly recommend and would definitely stay again here...:)
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Date of stay: March 2017Trip type: Travelled solo
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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Jawanza S wrote a review Aug 2016
1 contribution
I've found myself describing Two Seasons as a "humble hostel". The rooms are comfortable and include all the necessities one might need during their stay; fresh sheets, towels, fan and mosquito net. The host Dale, is an extremely friendly guy who has a great knowledge of the island and could easily give great suggestions of anything related to Tobago. The large balcony overlooking the Caribbean Sea is well shaded and is quite pleasant for relaxing at any time during the day. There is a restaurant called The Fish Pot located downstairs which offers excellent service and delicious flavours (one of the few restaurants to serve lionfish on the island!), otherwise there are fruit stalls, bars and other food stops all located within the area. If you're about learning the island from a local perspective, and looking for affordable accommodation, Dale's place Two Seasons just might be perfect!
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Date of stay: August 2016
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Trip type: Travelled on business
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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Emma H wrote a review Feb 2016
Moultonborough, New Hampshire2 contributions1 helpful vote
Hey everyone if you're planning on visiting Tobago Dale's place, Two Seasons, is the place to be. I had stayed at four guesthouses during my time in Tobago and this one topped them all. The rooms are so nice and comfortable, big beds, privacy, lots of places to organize your belongings, and a super cool mosquito net! That was awesome. Dale keeps you stocked with clean towels and sheets. There's a really cool balcony with an amazing ocean view, and t's just a real cool place to chill out with the other guests and have big dinners and drink rum :) Dale is an amazing host! He bakes the best bread on the island, and I'm not exaggerating ask any local they all know of his bread yuummmm:) He knows so much about the island and the plants, he taught us how to do an aloe cleanse which was really cool and always opened coconuts for us. Every day Dale would bring us aloe because we were getting sunburned. He made my time in Tobago feel like home and I cannot wait to be back <3 <3 Thanks Dale love ya! Oh yea and the beach is literally a 5 minute walk down the road which is sweet for the cheap price of the rooms, there's a restaurant right below the guesthouse, a bar and fresh fruit/veggie stand across the street and a bunch of food places within seconds of the guesthouse.
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Date of stay: January 2016
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Trip type: Travelled solo
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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dorit337 wrote a review Jan 2016
Germany4 contributions1 helpful vote
A simple, tidy and cheap residence to stay. You are in the middle of everything- restaurants and snack bars, a supermarket, a cash machine and a nightspot are around that place. From the big balcony you have a nice view to the ocean. The Mont Irvine Bay is nearby. Whenever you have a question just ask the kindly host. Here is the right place to enjoy the Caribbean feeling and to meet international and local people. You can find the Two Seasons Guesthouse on Facebook, too.
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Date of stay: December 2015
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Trip type: Travelled solo
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Mathieu Plante wrote a review May 2013
Montreal, Canada4 contributions6 helpful votes
The both hosts were very nice and helped us with all our needs. They are very kind and ressourceful. It is cheap, you don't go there for 5* rooms etc, but if you want to save on the rooms and have a good time with local people, this is a great place to start. we will definately be coming back! Mathieu & Kim
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Date of stay: April 2013
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Trip type: Travelled as a couple
Room Tip: Ask for A/C rooms in Trinidad if you don't like the hot weather to sleep!
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This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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Road99go wrote a review Apr 2013
Quebec, Canada1055 contributions412 helpful votes
You will find Two Seasons Surf at Mont Irvine and Two seasons in Trinidad working together. The one in Mont Irvine is situated over the restaurant The Fish Pot, own by the same person. You can find some rooms with bunk beds and some private with a commune balcony and a commune kitchen. Simple and friendly place rented by locals and tourist and close to the beach The renting is usually manage by the owner of Trinidad.
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Date of stay: March 2013
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Trip type: Travelled as a couple
Room Tip: Be sure that your reservation is Re-confirm
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This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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LOCATION
CaribbeanTrinidad and TobagoTobagoScarborough
NUMBER OF ROOMS
4
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TWO SEASONS GUESTHOUSE: See 8 Reviews, Price Comparison and 12 Photos (Tobago, Trinidad and Tobago) - Tripadvisor

Frequently Asked Questions about Two Seasons Guesthouse
Which popular attractions are close to Two Seasons Guesthouse?
Nearby attractions include Corbin Local Wildlife (4.2 km), Adventure Farm and Nature Reserve (3.7 km), and Argyle Waterfall (2.1 km).
What are some restaurants close to Two Seasons Guesthouse?
Conveniently located restaurants include Edge of the Reef, The Fish Pot, and The Seahorse Inn.
Are there any historical sites close to Two Seasons Guesthouse?
Many travellers enjoy visiting Fort King George (2.3 km), Fort James (4.8 km), and Courlander Monument (4.6 km).